nothing screams summer like chicago concerts under the stars We won't lie. Chicago summers are the best, but they're also way, way too short. So we have to make the most of those warm, sweet months when shorts and flip flops replace parkas and snow boots. And we do. Things kick off in early June with the FREE (yeah, that's right, free) Chicago Blues Festival, the biggest of all the festivals. Then summer kicks in to high gear with the electronic dance festival Spring Awakening. Don't miss the delicious Taste of Chicago in July, where the food is served up alongside great live music. Staples like Lollapalooza and the North Coast Music Festival keep you rocking through August and September. The beat goes on. And on.